Dating Lindsey Ch. 01

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
begger
begger
59 Followers

She put her hand over my crotch and felt the contours of it through my pants. She whispered to me, "Is it getting uncomfortable?" to which I could only groan and nod my head. She kissed my neck and said "Mom, can we take his cage off now? He's got to be getting snug in there," she said, giggling.

"Maybe on your next date, Lindsey,"

"Mom! Comeon," she whined.

"I didn't raise you to slut yourself about in college, dear," she said plainly.

"I'm not in High School anymore, mom, he doesn't have to stay in the cage the whole time. I don't want to have to wait for the second date just to see it."

Her mother sighed loudly. "I guess they all grow up," she said, giving in. "Fine Lindsey, but don't come crying to me when he dumps you for being a slut."

Lindsey rolled her eyes to me, and stood up. "I'll be in the bathroom."

I awkwardly walked over to her mom when she beckoned me and she started taking off my pants. "Listen, you better not get any ideas." She stripped my boxer-briefs down and instantly held my balls firmly, almost painfully in her fingers. "You might not be in that cage but I've still got you by the balls!" she said firmly, squeezing to make her point.

"Ohh, yes ma'am" was all I could say. She took her hand back and gave my balls a slap, eliciting a yelp from me.

"Hush," she instructed and slapped me again. "That's just a little taste of what you get if you even think of going too far with my Lindsey," she said giving me a serious look. I could only nod my head, feeling another slap hit my balls. I stood there, in pain, my balls throbbing as she leaned in to unlock the cage and slide it off of me. She gave my cock a look, watching as it hung half-hard in front of her. "Now pull your pants up and go sit down."

Lindsey came back and got even closer this time, putting a hand on my thigh and eagerly moving in for more making out. I put my hand behind her back and held her close as we kissed and I could feel her hand wander down over my crotch, feeling the bump in my pants back and forth. I moaned out, unable to help it and I could practically hear her mom's discomfort as her daughter rubbed my cock back and forth through my pants. She giggled, giving me a bashful look and whispered "it's big," and went in for another kiss. The words only made me stiffer, as I felt her squeeze my shaft, her fingers touching my balls through my jeans.

At this point I was getting very turned on, almost worried about losing control and making a mess as she rubbed me with much focus, enjoying the feel of my hardon under my pants. I was shocked as I felt her hand go under my shirt and then down into my jeans. I almost lost it then, as I felt her hand grasp and hold my cock. Her hand warm and soft, touching it, letting her fingers move gently along my sensitive skin. I groaned, feeling her fingers slide along it. She smiled bashfully, clearly enjoying how it felt and she gave me a look as she started sliding her hand up and down the shaft.

I squirmed and moaned. The pleasure of her hand awkwardly moving back and forth inside my pants was overwhelming. I had never been more aroused in my life and it was obvious she could feel it. She smiled at her own work, getting me worked up, making me need it. She bit her lip as she unzipped my pants, and tugged them and my boxer-briefs down a bit, revealing a very hard cock, standing straight up.

"Wow..." she muttered, putting a hand on my thigh, watching it throb and pulse against my stomach. "He's so hard mom, look," she said, giggling, poking me.

"Well you've been putting out for him like a common harlot."

Lindsey just laughed and smiled at me, grasping my cock again, squeezing it, rubbing it up and down a few more times. "You like that don't you?" she asked, running a finger down my shaft. I groan and shifted my weight, very aroused at this point.

"I won't say it isn't an impressive one, Lindsey. Certainly better than your last boyfriend."

"I know, like, half this, right?" she said with a snicker, bracketing her fingers halfway up my cock to show her.

"I'm so glad you let him go. I told you that you would find a better suitor. This one's nice, he's gentlemanly, and well...well endowed," she said, and I could see her blush as she looked over at me, obviously eyeing me up and down. Lindsey leaned in and whispered so her mother couldn't hear "I can't on a first date, but I just want to suck on it," she said and giggled softly, cupping my balls and rubbing the head of my cock, feeling it all over. Her mom only gave me a look, and I wondered if she knew what Lindsey had implied.

Lindsey's attention to my cock kept me hard and very close to the edge. She ran her hands over it, kissing me, sometimes paying attention to the movie, but she never stopped paying attention to my needy cock, throbbing and frustrated now. My head swam as I saw her take notice every time my cock showed signs of going down, and she would quickly stroke me back to full strength, a process that she repeated several times, each one making me more and more needy for it.

I gripped the futon cover as I felt her stop right at the brink of orgasm, taking her hand away casually to keep me from blowing. I groaned, frustrated.

"Careful Lindsey," her mother warned.

"I am..." Lindsey said defensively. "He's not even close."

"Oh honey, he is very close," her mom said, eyeing my throbbing cock. "Just look at those full balls. He is primed and loaded," she said covering her mouth at her off-color joke.

I swallowed hard, embarrassed at these two women talking about my cock and balls. Lindsey cupped my nuts, and felt them, squeezing and moving them around. "Wow, these are getting full," she said with a smile to me. "Been enjoying yourself?"

I could only nod, precum coating my cock. She stroked me a few more times and I squirmed, wanting it so bad. "Oh..." I moaned out, feeling my balls tense, my cock aroused.

"Lindsey..." her mom said, in a scolding tone.

Lindsey sighed and looked down at me, hard and throbbing. She ran her hand over it a few times. "Well I guess the movie is almost over," she said, trailing off, feeling me throb against her fingers. "I guess we can put it away."

I gulped. "What...what do you mean?" I asked.

"Well, it's late, the movie is over. I had a really nice time with you tonight. I hope...I hope you ask me out again," Lindsey said with a smile.

"Oh, yeah definitely. I want to go out with you again, too," I said holding her hand.

"How darling," her mother said in what I wasn't sure was sarcasm or not. "Time to lock him back up, Lindsey," she said coming over.

"Wait...but..." I said, unsure, as her mom sat next to me. Lindsey looked at me curiously.

"You didn't think you were getting a...well you know...on the first date did you?" her mom said, giving me a cold stare.

"Well no...but. I mean of course not, but we don't need to put me back in it. I was just about to leave," I said, worried as I saw her mom getting the cage out and opening it up for me.

"And that's exactly why we're caging you. We can't have you going home and doing...what all college boys do when they get home. I'm amazed they don't have to clean out the pipes daily," she said, shaking her head.

"Wait...but you can't send me home in that thing," I said, looking to Lindsey.

Lindsey just smiled at me. "Don't worry. It's not like you're the kind of guy that does that anyway," she said, putting a hand on my thigh.

"No you're not, are you," her mom said, with a knowing look to me. "You're a nice boy who would never jerk off after dating a nice girl like Lindsey huh?"

"Um...no...I guess not," I said sullenly, only making her mom smile more.

"Good for you," her mom said, and cupped my balls. "Now just relax big boy and I'll use an old trick to get you into this cage."

Lindsey only smiled, naïve surely as her mom squeezed and crushed my balls in her hands. I squirmed and yelped but Lindsey just comforted me as I felt my balls compressed with almost machine-like strength. Her mom squeezed until I went soft, or at least soft enough and then I felt her slide the cage back onto me.

Lindsey kissed my cheek and touched my chest as her mom locked me in place, with a little too much arrogance for my liking, but there was nothing I could do. I wanted another date with Lindsey, and I didn't want to mess up the first opportunity I'd had to get with a girl in a serious relationship. So I let them pull my pants back up, my balls aching a lot more than I'd ever been used to. I don't know if I'd ever had blueballs before, but you certainly know when you have them. After so much teasing, I could barely walk they ached so much.

I tried to be as polite as I could, and kiss Lindsey goodbye. Now locked up, her mom let us outside of the room alone. I kissed Lindsey a few more times.

"I had such a good night you with you, Jake. Will you really take me out again?"

"Yeah, definitely," I said to her, butterflies in my stomach.

"Ok, good!" she said, with a big smile. "Um, Facebook me or text me or something ok? I can't wait to see you again."

I smiled and gave her a parting kiss. I watched her head back to her room and could only wonder what Lindsey and her mom would talk about. I walked back home with a painful set of blueballs, and it wasn't till I got back in my room, and into the bed, when I truly realized how stuck I was.

begger
begger
59 Followers
12
Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
5 Comments
goodslave4ugoodslave4u1 day ago

I really liked the story.... great job... hope you keep it coming.. but after all this time I guess you lost interest???

AnonymousAnonymousover 5 years ago

And really her mom wouldn't start fondeling him like that. I completely skipped that part. This not even close to being realistic in the slightest.

AnonymousAnonymousabout 11 years ago
Idiotic

In the first place the answer is NO - you can't put that thing on me. In the second place, it always amuses me that anyone believes that you could actually keep someone in a cage. Short trip to the hardware store and 1 minute later the cage is history. Hint - the hasps are the weak point, end dykes cut them easily. A Dremel will cut off any lock. All done and all done with this unbelievable story. And if she is going to treat you like that, why would you stick around for even a minute? Answer - no one would.

AnonymousAnonymousabout 12 years ago

Love it, thanks.

AnonymousAnonymousabout 12 years ago
AWESOME!!

Can't wait for the sequel!! Hurry up plz!!

Share this Story

READ MORE OF THIS SERIES

Similar Stories

Teased and Denied Ch. 01 Dominant wife controls willing husband's orgasms.in BDSM
Milker Pain Rachael milks her boyfriends with a machine after chastity.in NonConsent/Reluctance
John and Erin John learns to please his dominant girlfriend.in BDSM
White Raven Pt. 01 A young couple experiment with tease and denial.in Erotic Couplings
Chastity Resort Pt. 01 My wife agrees to a nudist resort, but on her terms.in Exhibitionist & Voyeur
More Stories